Did I “Win” The Breakup?

This week, J & J are fresh off a dinner party together, but Jared’s own awkward encounter at a bar afterwards has him regretting that nightcap martini. After some daydreaming about winter getaways, we dig into the e-mails, starting with a listener who put their friend onto the pod, watched them succeed at finding love, but keeps striking out on their own. They tackle a couple of listener’s dating app woes, like should you stop replying if they make an edit to their profile you really dislike? Today’s "Awkward Encounter" pushes the boundaries between “awkward” and “heartbreaking,” with a write-in from a woman who thought she was getting a ring but got a break-up instead. Keeping the New Year unhinged, “Red Flag or Deal Breaker” covers disclosing food allergies, being pushy about “going to my place”, and talking about your parents sex lives on a first date… which we think might require a little more professional help. Learn more about your ad choices. Visit megaphone.fm/adchoices